Jeeves would have been the one to schedule the anthem singing and would have given you the choice of a couple suitable outfits for the occasion. Or just packed both the tuxedo and the jeans. If someone's flying you out to sing, you probably are in first class and have the upgraded baggage allowance.
The mistake you imagine is exactly the kind of thing competent human assistants are good at avoiding and AI is terrible at.
Jeeves is my butler, not my executive assistant and presuming otherwise will get Jeeves fired as well.
Competent human assistants know to negotiate formally or informally with their employers the limits of their authority. Unfortunately those creating products either do not know or do not care to negotiate clarity on such limits, and end up like poor Jeeves.
The mistake you imagine is exactly the kind of thing competent human assistants are good at avoiding and AI is terrible at.